HCID 22645937, compound → HCID 22645936, compound

HRID 2414459Notes

Reaction equation

HRID 2414459 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:3]1>[Pd]>[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:3]1

Participants

3

Reactant 1

HCID 22645937HCID 22645937, compound

Product 1

HCID 22645936HCID 22645936, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Starting from the compound N-(4-oxochroman-2-ylmethyl)acetamide 1, the carbonyl group is hydrogenated to the hydroxyl group with noble-metal catalysis, for example using Pd on carbon (50% water-moist), to give the compound N-(4-hydroxychroman-2-ylmethyl)acetamide 2. The acetyl group is cleaved off using a base, for example sodium hydroxide. Addition of an acid gives the acid-addition salt 3 of 2-aminomethylchroman-4-ol. A further noble metal-catalysed hydrogenation generates the acid-addition salt 4 of 2-aminomethylchromane.

Sources & evidence

ORD record
ord-810b8fcc091543d7b0b6c1a7db75293b
Source dataset
uspto-grants-2004_11
Patent number
US06812353B2

Reaction notes

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